Looking Back At My Year of Writing

A common theme emerges yet again — I spend most of the year feeling like I should be writing more and when I finally gather up all my public writing for this end of year article I’m pleasantly surprised by how much I actually wrote. I’m starting to think that mismatch between my expectations and reality may be more of a permanent fixture than I’d like.

Looking back at the writing I did for SamSpurlin.com I see a renewed interest in trying to write about my experiences with personal experimentation. I started the year by sharing how my Focus Months were going. And then again at the end of the year I started writing about my foray into weekly experimentation. This is something that’s likely to continue into 2021 and beyond. Instead of being embarrassed at how introspective and specific to me exercises like that tend to be, I’m going to challenge myself to write them in a way that is both interesting and useful to other folks. No more shying away from the weird things I do that I personally think are interesting.

Beyond the personal experimentation recap articles I also got down some key ideas that I’ve been wanting to explore for a long time. Namely, the idea of personal development being an exercise in exploration (or an expedition, as I call it in the article) and the basics of my system for “deliberate personal development.” These are related ideas that I’ve only just started poking around the edges of. These will likely make an appearance in 2021, too.

SamSpurlin.com

1. Looking Back at a Year of Growth, Grief, and Calm

2. The Year of Intensity/Simplicity

3. How to Engage With an Overwhelming World

4. Introducing Focus Months

5. In February I'm Going to Write a Shit Ton

6. The End of My First "Month of Write"

7. "Month of Sit" Recap & a Look at April

8. Personal development is an expedition, not an exercise in perfection

9. Carving Out Your Space to Contribute

10. Recapping My Second "Month of Write" and Looking Ahead to a "Month of Read"

11. Exploring the hard reset

12. Trying to understand my resistance to second brains, digital gardens, and other interesting note-taking concepts

13. Experiment #1: Do The Work Before Wallowing

14. Experiment #2: Green Tea is the New Coffee

15. Experiment #3: Sustain the Home Routine

16. Experiment # 4: Morning Meditation

17. My System and Method for Deliberate Personal Development: An Introduction and Overview

The Deliberate

Thirteen issues means I put a new one out at a little over one per month. If I had conceptualized this as a monthly newsletter then I’d be thrilled. For some reason, though, I’ve always thought of this project being weekly in nature (or maybe biweekly, at most). I don’t think I’ve ever stuck to that cadence for more than a couple weeks so it might be time to face the music and admit to myself that this is never going to be a weekly newsletter.

I think I’m okay with that.

The main thing I like about having a newsletter is that it makes me more attentive to the things I’m seeing and reading. When I’m regularly writing I find myself engaging with the world from a posture of readiness. “Is this something to write about? Is this something worth sharing? Oh! What about this thing?” When I’m not regularly curating and writing the newsletter I can find myself floating through the world in a much more passive mode. Interesting ideas just kind of slide off my brain and don’t find anywhere to latch onto. It’s more tiring to be in that active frame of mind but it’s also much more satisfying than the alternative. 

If you’d like to follow along with The Deliberate in 2021 be sure to subscribe.

1. Why All The Tracking? (TD #27)

2. How To Deal With an Overwhelming World (TD #28)

3. Digital Declutter 2020 Edition (TD #29)

4. Things Fall Apart (TD #30)

5. Sitting and Writing and Quarantining (TD #31)

6. Bottom Up Personal Development (TD #32)

7. Extracting Some Insights From a Down Week (TD #33)

8. Making Space to Write (TD #34)

9. A Checklist For When You Feel Bad But You Want to Stop Feeling Bad (TD #35)

10. Exploring the Hard Reset (TD #36)

11. The Privilege of Extra Unused Attention (TD #37)

12. Clearing the Decks (TD #38)

13. Frivolous (TD #39)

If you found yourself reading and enjoying anything I wrote this year I want to thank you for giving me some of your time and attention. I tell myself that I mostly write for the intrinsic enjoyment and meaning that I’m able to derive from it but I’d be lying if I said I’m immune to feedback. I love when people share what I’ve written, send me an email, say hello on Twitter, or any other avenue of communication. 

Thanks for keeping me going during a weird year.

My System and Method for Deliberate Personal Development: An Introduction and Overview

For as long as I can remember I’ve always been overwhelmed by the number of things I wanted to do or try. As a voracious reader of personal development books I seemed to have a never ending torrent of good ideas raining around me at all times. Ideas about how I could be better. Ideas about new habits to start or stop. Ideas about how to build a life that I’m proud of. Being the overachiever that I am, I would find myself trying to do all the things all the time. I wouldn’t ever consciously stop one personal development intention and start a new one because I never got super clear about what I was actually trying to do. I would just let all these good intentions and good ideas kind of wash over me and because I am not some kind of prodigy this would obviously always mean I was failing on at least a handful of vague intentions at the same time. Instead of feeling like I was making and keeping commitments to myself I was always operating under a vague sense that I wasn’t doing the things I said I wanted to do (even though, overall, I was definitely doing a lot).

Eventually, I homed in on two key concepts for the system I ended up developing for myself: limiting work in progress (WIP) and iterative experimentation.

As anyone familiar with the Theory of Constraints knows, putting a cap on the number of things that are allowed to be “active” at once actually increases the flow of items through a system. If you have a backlog of 10 items you’ll actually complete them faster if you only work on 1 or 2 at a time, rather than trying to chip away at all 10 simultaneously. In the case of personal development, we don’t actually care about finishing things quickly — but we do care about finishing things (which is really more of a psychological state than anything else). The power of this idea was fairly obvious to me in a work or school context, but I started to wonder if it applied in a broader personal development context, too. 

Secondarily, as I got deeper into my work with organizations through my job at The Ready I came to better understand the power that continuous experimentation can have when a team is trying to do something new. While I had always been interested in self-experimentation, especially as part of the quantified self movement, I developed a new appreciation for what disciplined and iterative experimentation looks like and what it can unlock through my work at The Ready. I started to apply this experimental mindset to my own personal development endeavors with really surprising results.

The combination of limiting WIP and adopting a habit of continuous experimentation was what helped me start to feel good about my personal development efforts for the first time. In the rest of this article I will show you the system I developed for myself as simply and directly as possible.

The goal is to create an external system that can hold all the ideas for potential experiments you get from the world around you (books, podcasts, etc.), help you develop those ideas into full-fledged yet tractable experiments, help you limit the number of experiments you are pursuing at once, guide you in learning from the experiments you’ve done, and help you uncover the core personal insights that are the ultimate goal of the whole endeavor. 

The Tool

It sounds like a lot, but a relatively simple Kanban board can do most of the heavy lifting for us.

A Kanban board is a tool that helps you visualize work and the various states in which it could be. The simplest version has three columns: To Do, Doing, and Done. We aren’t going to complicate it much more than that.

Our Deliberate Experimentation Kanban is going to have the following columns: Inbox, Backlog, Active, Done, and a separate, but related, area called the Insight Library.

Inbox

This is the list where you can throw any vague idea or intention to ensure you won’t lose it. You haven’t committed to anything that’s on this list. It’s simply the top of the funnel for things you might want to potentially do. Anything can go in here. Musings, questions, thoughts, a word or two... anything to get the thought off your mind and into the system.

To Do

When you move something out of the Inbox because you’re pretty sure you want to do it soon, you move it to the To Do list. Here you’ll fill out the Basic Experimentation Template and make sure you’ve thought through the details. These ideas are ready to go... but aren’t active yet.

Active

This is where you put the experiment you are currently doing. Every day you’ll check-in and add relevant data or reflections to the card. Ideally you won’t have more than 1 or 2 experiments active at a time (remember, limit WIP!).

Done

This is simply where you put the experiments you have completed. In order to move an experiment from Active to Done you need to fill out the End of Experiment Retrospective questions. This is where you’ll make sure you extracted all the lessons — and maybe even extract an Insight or two!

Insight Library

The last part of the system actually lives outside of the Kanban board itself as a separate document that I call my Insight Library. The whole reason we’re doing personal experiments is to uncover these key insights about ourselves. We’re systematically trying new things so that we can systematically explore our beliefs, assumptions, and abilities — all the stuff that makes up who we are as people. It’s about uncovering, discovering, and maybe even changing, more and more of our identity over time. As we do more experiments we will capture new insights about ourselves or adjustments to insights we’ve made in the past. This slow but deliberate accrual of our own personal Insight Library is personal development.

The Routines

A Kanban board is not enough... it must be paired with a few key routines related to how we use the tool.

First, there’s the ongoing habit of throwing ideas into your Inbox as you come across them. It’s being able to notice when you’re thinking, “I should try...” or, “I wonder what it’d be like to...” and capturing those ideas into your system as soon as possible. Sometimes these ideas will pop up out of thin air and other times you’ll capture them as you read a book, watch a YouTube video, or have a conversation with a friend. They can come from anywhere and the more you practice the better you’ll get at capturing them right away.

Second, there’s the daily routine of reflecting on how your active experiment(s) is going. I usually do this in the evening before I go to bed. It’s as simple as logging into your Kanban and tapping out a sentence or two about how it went today. Sometimes, if the experiment is extremely cut and dry, logging the day’s data is as simple as writing “Yes” or “No.”

Third, there’s the weekly routine of retrospecting on the whole experiment (assuming you ran the experiment for a week — some experiments are longer than that). This is where you pause and ask yourself some general questions about what went well, what didn’t go as well, and what you learned.

Finally, there’s the trimesterly(ish) routine of going through all your completed experiments and mining them for potential Insights and new experiment ideas. Sometimes you need to accrue many weeks of experiments before patterns and themes start emerging. A lot of the time you’ll notice them without having to do this quarterly routine but I like to schedule some time every 4 months or so to do a deep dive into my completed experiments to see what I can find.

It sounds like a lot, but generally each of these can be done in only a couple minutes. Setting up some automatically recurring reminders and building them into your overall routine makes them something that you’ll learn to look forward to over time.

What else do you want to know about this system? What isn’t clear? What doesn’t make sense? I intend this to be the beginning of a lengthy series expounding on this approach and your feedback will help me better understand where I’m not clearly describing what’s in my head. Let me know on Twitter (@samspurlin) or in the comments below!

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Curious to learn more about this system as I experiment with it in real time? Join my newsletter, aptly called The Deliberate, to get behind-the-scenes writing and thinking.

Experiment # 4: Morning Meditation

I don’t have a dedicated place in my day for my meditation practice. When I manage to do it, it seems to be in the evening and it always feels like I’m somehow getting lucky. Other daily habits have places in my daily routine where they feel natural and good. I’d love to figure out what that could be for meditation and I’m wondering if it might be right after I wake up? 

I learned a couple weeks ago that I’m not as reliant on coffee as I thought I was so I think I could get up and meditate right away and then go into my morning coffee routine. As silly as it sounds, I’ve struggled with meditation right after waking up in the past because I couldn’t figure out the order of operations with my coffee routine. Option A is making coffee and then not drinking it for twenty minutes while I meditate. Meditation is difficult enough as it is... smelling coffee and knowing that it’s waiting for me the whole time feels like doing it on Hard Mode. Option B is making a cup of coffee, drinking it and then meditating. This seems rational but at that point, roughly thirty minutes later, I’ve kind of lost the “wake up and meditate right away” vibe and more often than not it’s difficult to put down whatever I’m reading and go do a harder thing (i.e meditate). Option C, which always seemed too hard, was to meditate immediately and then go make coffee after finishing the session. That’s the version I’m going with for this experiment.

For the next week, as soon as I wake up and use the bathroom I’m going to immediately do the twenty minute Daily Meditation in my meditation app of choice before doing anything else in my day (including making coffee). Under normal circumstances this means I’d be cutting into my morning reading time. In vacation mode, I don’t really need to worry about that. If it goes well, I can cross that bridge when I re-enter real life in January.

So, how did it go?

A week later and here I am. I successfully meditated for seven days in a row but I did not do each of those sessions immediately upon waking up. I think I managed to do that for five of those sessions. A couple things worth noticing:

• Somehow I went to bed a couple times this week with my phone sitting on the table next to my bed — which is not how I normally operate. On those occasions I found myself scrolling through Twitter in the morning rather than immediately getting out of bed and putting my butt on a cushion.

• Broadly, I noticed it can be tougher to get out of bed and get moving when the first thing on the docket is twenty minutes of meditation. Usually, making a hot cup of coffee is my animating force.

• That being said, I felt good when I did the morning meditation. A nice mix of calm, focused, and accomplished.

• I think this is probably the best spot in my day for meditation to live. I’ve still got a long way to go to make it feel automatic but I at least showed myself that it’s possible.

Experiment #3: Sustain the Home Routine

I’m in Florida for a month without my stationary bike — my primary source of exercise — and I need to figure out another way to burn some calories and keep myself mentally healthy. Normally I’d go for 30-60 minute ride a couple times a week as my primary means of exercising (in addition to a very low-key morning walk which is much more about waking up than it is about getting stronger). If I was only going to be here a week or two I wouldn’t worry too much about it but because I’m here until early January I don’t think it’s wise for me to throw all plans of exercise to the wind and just roll with the punches. Because I will end this month too fat. Fat and sad. And nobody, especially me, wants that.

And really, it’s about more than exercise. Without going into a bunch of detail that makes me look even more privileged and out of touch than I already am, I’m fortunate to be spending the month of December in Florida with very little work to do. Emily and I drove down (to avoid the Covid hotbeds of airports and airplanes) and are socially isolating in a condo that we’re inhabiting by ourselves (and we just got tested for Covid today). I’m very lucky to be able to do this. And I very much need the break. But four weeks is way too long to be in “vacation mode” the whole time.

So, to preempt that, I’m calling this week’s experiment Sustain the Home Routine. It’s about hitting the same major beats of my daily routine at basically the same time and not throwing all my structure out the window just because I’m in a new location and a non-work setting. It would be very easy for me to ignore all the routine that I rely on and love when I’m in more “normal” times just because I’m on vacation and in a new location. Without a little bit of vigilance I’ll eat like an idiot, exercise not at all, and just kind of flit from one somewhat pleasing activity to another before ultimately ending the day not feeling particularly rejuvenated or good.

More specifically, these are the basic “beats” of my day that I’m expecting myself to adhere to for the next week:

• 6:00 up, make coffee, and read a book

• 7:00ish out the door for a walk

• 9:00 - 12:00ish knock out whatever work I need to do

• 12:00ish lunch that I make (not delivery or fast food)

• 3:00ish snack so I have enough energy for an afternoon workout

• 5:00ish some kind of workout, probably a run

• 6:00ish make dinner

• 7:00ish dinner

• 10:00ish bed

What may seem like a ton of structure to some is actually the perfect scaffolding for me. It ensures I’m doing the most important stuff without hyper scheduling my day (especially since I’m ostensibly on vacation). I’m hoping that this little bit of extra planning and discipline will actually make me feel more rejuvenated than if I just followed each and every whim that I have.

End of Experiment Retrospective

The experiment this week was to basically hold onto the normal beats of my daily routine even though I’m in a different location and ostensibly on vacation. A month is too long to be in full-on vacation mode and I know I’m the type of person who derives a lot of comfort and satisfaction from keeping to a relatively consistent daily routine.

 How did I do? I’m going to give myself a letter grade for each of the areas I said I wanted to focus on:

• Waking up & going to bed on time: Pretty much nailed it. Got up a couple minutes late (like, < 10 minutes) a couple times but that’s a pretty negligible miss. A-

• Going for a morning walk: 7:10, 7:06, 7:04, 10:52, 7:10, 12:10 were the times of my morning walks this week. The 10:52 day I deliberately decided to go later because I was down to the last few pages of a book I had been reading for a long time. The 12:10 walk was on Saturday and I’m deliberately much more relaxed about when things happen on the weekend. A

• Make lunch rather than buying: Made lunch every day. Booya. A

• An afternoon snack: I don’t keep records of this so I don’t know exactly how I did. I’m guessing pretty well because when I get my 3:00 PM reminder on my phone I get SO PUMPED to eat a snack. Snacks are the best. Probably an A?

• An evening workout: I’ve been trying to do a bit of a run/walk as my workout. I haven’t run in months so it has been very slow going. More walk than run, if I’m being honest. I made it out there on Monday, Tuesday, Wednesday (active recovery), and Friday. The only day that felt a little bit like a miss was Thursday, but honestly my body was not feeling all that great so I think the extra rest day was smart. Nothing on Saturday other than a bonus walk (on the beach). A-

• Making dinner rather than buying: Nailed it. We did a great job using our groceries this week. We even skipped Friday Pizza Party in favor of an equally fun dinner we made ourselves. A

Overall, I call this experiment a resounding success. I definitely felt pretty good and didn’t get into that listless state where I find myself kinda mindlessly drifting from one distraction to another for large swaths of the days. That’s always enemy #1 for my happiness so experiments that help me keep that at bay are very much worth it. As I suspected, a decent daily routine gives me something to build around and as long as I don’t become an utter slave to it, then I think it’s a mostly positive thing for me to focus on — even on vacation.

Experiment #2: Green Tea is the New Coffee

Sometimes personal experiments are extremely connected to deep and important changes I want to make in my life. This is not one of those times. This is going to be an experiment borne of two parts logistical necessity and one part morbid curiosity.

I’m not a huge coffee drinker, in volume, but I am a huge coffee drinker, in love. I love fancy fresh beans. I have a fancy electric kettle with a gooseneck that allows for precise pouring. I use an AeroPress. I drink two cups every morning and almost never exceed that.

That being said, I’m pretty sure I’ve had at least one cup of coffee every day for like… 15 years? Longer than that?

I don’t like knowing that I’m reliant on a drug to feel good in the morning and I’m curious what it’ll be like to not drink coffee for a week. Also, I messed up my coffee delivery subscription and I’m currently out of coffee until Wednesday. But I did just buy some very nice green tea that arrived late last week.

For the next week I’m going to replace my two morning cups of coffee with green tea.

Hypothesis: I’m going to miss coffee a lot. I’m going to feel kind of bad. But by the end of the week I’ll have worked through whatever caffeine withdrawal I might be feeling and I’ll be proud of the hard earned self-knowledge I’ll have gained. Or something like that.

End of Experiment Retrospective

This went wildly better than I expected.

Monday night’s sleep.

I thought that because I love my morning coffee routine so much it would be a total drag to not do it for a week. Luckily, it looks like my two cups per day habit isn’t enough for me to be hopelessly caffeine addicted.

Monday night (the first evening after replacing my morning coffee with green tea) was the only time I really felt any negative physical symptoms. A nice dull headache settled in by the afternoon of that first day and I felt absolutely wiped by 8 PM. I dragged ass until 9 PM before deciding to just give in to the inevitable and hit the hay. I then slept hard.

The rest of the week I went to bed and got up at my normal times (10 PM/6 AM). I didn’t feel terrible in the morning and I was able to go through my day feeling fine.

So, the takeaway from this isn’t that I’m now going to give up coffee. Instead, I’m going back to my morning coffee routine feeling much better about it. I know now that I’m not hopelessly addicted to caffeine. I just like coffee and I like the ritual of making it my fussy way each morning. It’ll feel nice to go back to it knowing I can drop it again without crushingly adverse consequences if I ever need or want to. I have a feeling that’ll make it taste that much better.

Experiment #1: Do The Work Before Wallowing

Sometimes I get extremely wrapped up in my own head about all sorts of things. I start doubting whether I’m any good at my career, whether my clients secretly think I’m doing a terrible job, whether I should quit my job and go do something completely different. I start beating myself up for not writing more or reading more.

It’s okay to feel bad sometimes. Honestly, sometimes feeling bad is the pre-requisite to feeling really good later. But I don’t like feeling bad for seemingly no reason.

Over the past few years I’ve done a pretty good job finding the minimum viable habits necessary to have a decently high probability of having a non-terrible day. Doing these habits doesn’t guarantee that I’ll have a good day but it almost guarantees I won’t have a truly dismal day.

What’s silly, though, is that I’ll sometimes find myself circling the psychological drain without having yet completed my daily habits (what I call my Anchor Habits and which consist of doing some sort of minimal deliberate exercise, reading at least fifteen minutes of a book, meditating for at least ten minutes, and doing one session of any length of writing). How can I look at myself in the mirror and say, “Yep, this is some righteous wallowing,” when I haven’t done the things I know tend to make me feel better?

If I notice myself wallowing without having completed my Anchor Habits, I must complete my Anchor Habits before resuming wallowing. If I’ve done my Anchor Habits and I still feel like shit, well, that’s how it goes sometimes.

End of Experiment Retrospective

Key Stats

• Number of “Anchor Days” (days where I completed all four of my daily habits): 4 (the last time I had at least 4 Anchor Days it was August and the last time before that was April)

• Total Anchor “Points”: 22 out of a possible 28 (average YTD is 18)

I didn’t mention this in the setup for this week’s experiment, but there was a pretty huge confounding variable that surely messed with my experiment a bit this week — a very short work week and the Thanksgiving holiday. This was obviously a pretty atypical week so I don’t know how much of what I experienced can really be attributed to the experiment. That being said, subjectively it seemed to help. I did a pretty okay job actually “doing the work” (doing my four daily habits each day) this week and I felt pretty good all week. I didn’t actually record any data about how I felt at the end of each day, so this is entirely subjective and likely biased by how I’m feeling in this moment as I’m writing this, but overall it felt like a pretty psychologically healthy and overall positive week.

As always, the two Anchor Habits I was least consistent with were Writing and Meditating. Neither one of these has a really locked-in time slot in my daily routine like Reading and Exercise do. I did start to circle 9:00 PM as my meditation time and having it be the last thing I do before I get ready for bed. Writing seemed to mostly get slotted into the after dinner time slot (when it happened at all) … but it was pretty inconsistent. In my ideal world I would give more of my “prime” hours (i.e. the morning) to writing so I don’t always feel like I’m scraping the bottom of my energy and motivation barrel when it comes time to write.

I consider the experiment a success and while I’m not going to officially do it again next week, this is an example of one of those experiments where I intend to more or less keep it going indefinitely even though I wanted to focus on it intensely for a week to help get it going again. The whole point of having daily Anchor Habits is that I do them every day. The key thing, though, is remembering to ask myself if I’ve finished my Anchor Habits for the day if and when I find myself in a psychologically dark place again.

Trying to understand my resistance to second brains, digital gardens, and other interesting note-taking concepts

All the coolest kids are building “second brains” and “digital gardens” and public note-taking libraries and I’m sitting here like a rube with no robust note-taking system. I am one of the most knowledge worky of all knowledge workers — a management consultant. I mostly spend my days having conversations with executives about how their organizations can be better, with teams who are trying to constantly evolve the way they work, and occasionally writing things that support both of those endeavors. And in my “off time” I try to write semi-insightful things on this website and in my newsletter. If there’s anybody who could benefit from having a note-taking system that generates insights that can be turned into smart words (spoken or written), it’s me.

And yet, I don’t. And I don’t think I’m going to any time soon.

The cynic and small mean person inside me sees these folks expounding the value of their digital gardens and wonders if they’re missing the point. I don’t actually follow any of them closely enough to know if this is true (it’s probably not) but if all the work being put into the note-taking system isn’t resulting in actual outputs then it seems like misplaced effort. It’s like a chef collecting a huge library of impressive and rare ingredients but never actually making anything with them.

My process is a lot more like coming home from the grocery store with the ingredients in hand and basically immediately turning on the stove and getting to work. I know that if I don’t capitalize on the motivation and the available ingredients when they are easily at hand I’m unlikely to do much of anything with them. The optimist in me says it makes me very efficient and somewhat, if sporadically, prolific. I suppose a critic would say that this process encourages a level of superficiality enforced by immediacy. How nuanced and expansive can I be if I don’t have a place for ideas (ingredients, maybe? I’m letting this metaphor get away from me) to go ferment for awhile. Other than my brain, that is. My first brain, not a second one.

Perhaps I’m not giving myself enough credit for what I do. I may not have a digital garden, but I do have a digital windowsill with a couple herbs sitting on it (I will wring every bit of utility out of this metaphor; just watch me). I have what I call my “Spark List” which is a simple text file with every scrap of an idea that I’ve ever had that I think I might want to write about at some point. When I want to write but don’t have something sitting at the front of my awareness I’ll sometimes go shopping in my Spark List for something to write about. 

I’ll also do stream of consciousness writing about a variety of topics and they almost always get saved in Day One which is ostensibly a journal but has really become a catch-all place to store writing that doesn’t have much of a home anywhere else. It doesn’t get any meta-data attached to it other than the date at which I put it into the program. Once every few months I’ll go through Day One and read those entries and see if it sparks anything to be added to the Spark List. Otherwise, Day One gives me an “On This Day” notification every morning that shows me everything I’ve saved in the program on the given date since 2011 (which is when I started keeping a journal). Mostly what I’ve learned from this is that I’ve been thinking about and struggling with the same things for the better part of a decade. Something to be said for consistency, I guess?

I look at what people have built with Roam and I think, I should do that. I look at what people are doing with Notion and I think, I should do that. I look at what people have made with DEVONthink and I think, I should do that.

For now, though, I’m going to keep the shortest distance between inspiration and output as possible. That’s the best way I know how to work and diving deep into the world of note-taking sounds exactly like the kind of productive distraction that would keep me fat, happy, and distracted for months while I never actually make the things that the notes are supposed to support. Maybe all those years of writing the same things into Day One have taught me something about myself after all?

Exploring the hard reset

I’m no computer expert so I’m not exactly sure what causes them to periodically lock up and require a hard reset — holding the power button down for an uncomfortably long time and interrupting whatever runaway process or hopelessly locked instructions is causing a computer to be completely unresponsive. I’ve always imagined the computer being a little bit concerned but also grateful that I’ve come along to release it from whatever is ailing it. A chance to start over, get rid of the extra stuff that is causing the slow down, and re-engage with the world with clear memory, greater simplicity, and a newfound sense of optimism.

That’s kind of what I’ve been doing to myself for the past couple weeks.

For reasons old (my compulsion to always do more and better) and new (a worldwide pandemic that has thrown a wrench into every plan and routine) I’ve been feeling a bit like the computer that is sluggish and verging on unresponsive. Inching closer and closer to where the usual troubleshooting actions are no longer effective and instead needing someone to hold my power button down until the screen flashes black and the normal boot up sequence starts again. Too many processes running at the same time. Too many open loops competing for the same limited memory resulting in a user interface that feels like it’s being dragged through mud. Like trying to stream a video through dial-up — stuttery, pixelated, and generally an unpleasant mess to interact with. 

Moving beyond the computer metaphor that I only understand enough of to barely muddle my way through, I recently realized that my 2020 theme of Simplicity/Intensity has been heavily weighted toward the Intensity end of that duality. Each month I’ve been taking a habit and trying to be deliberately intense about it. So far, though, I haven’t done much to explore the simplicity or spaciousness that I wanted to temper the intensity that tends to come more naturally and be more interesting to me. 

So, even though I’m still in the midst of my first Month of Read, I’ve also been experimenting with scaling way back across many different aspects of my life. Scaling back the number and complexity of the tools to do my basic work. Scaling back the number of open loops I have running at any one time. Scaling back the expectations and the negative self-talk that push me toward greater achievement while simultaneously making me unhappy. Scaling back the number of places I appear online and the number of feeds that need tending. It has meant looking at everything around me and asking myself whether I could do without something, at least for a little bit, just to see what it’s like. 

And although I’ve done a lot so far the process is still ongoing. Shedding the obvious dead weight results in new layers of things to consider. Things that weren’t obvious at first glance are brought into the light and analyzed for the first time. Old projects, old intentions, and old personal commitments that haven’t been re-examined or updated by the current version of myself. Old identities and expectations that no longer serve their intended purpose and instead are just consuming limited mental RAM.

The idea is not to move forward indefinitely as some kind of modern ascetic (I’m pretty sure the fact that I’m typing this on an iPad while living in an expensive apartment just outside of Washington DC prevents me from authentically claiming that path anyway). It’s more like a systematic dismantling of as much of the scaffolding I’ve intentionally and unintentionally built around myself over the last few years so I can better see the building — the person — underneath it all. When I was living in NYC there were certain construction sites that I only ever saw with scaffolding draped all over them. Scaffolding so dense and so seemingly permanent that it seemed to be an actual part of the building. And then, suddenly and dramatically and without warning, I would find myself walking the same path as always only to realize that somehow, improbably, a new building stood where before I usually saw the accoutrements of construction. Overnight the fundamental appearance of a building would change as the scaffolding was removed and the construction equipment moved away.

And there was almost always something beautiful standing there.

My personal construction project isn’t completed (and I don’t think I ever want it to be) but it’s time to take stock of what’s there before moving on to new projects. I’m hoping removing the detritus will give me a better appreciation of what’s already there and some new motivation to embark on the next phase of whatever it is I want to do. 

Recapping My Second "Month of Write" and Looking Ahead to a "Month of Read"

In February I conducted my first Month of Write and was very disappointed. In April I decided to take another crack at it quicker than I had initially planned in order to see if I could get the bad taste of February out of my mouth. Whereas in February I didn’t really have a plan other than “write more,” in April I specifically wanted to see myself get up at 6:00 AM everyday, sit down at my iPad or computer by 6:15, and write consistently from roughly 6:15 to roughly 7:30 (I originally intended to do 7:45 but quickly learned that that end time unnecessarily complicated my mornings).

As you might expect, April went much better than February.

First, a few objective stats:

• Words Written: 17,702 (compared to 6,500 in February)

• Days Written: 18 (compared to 13 in February)

• Published articles/newsletters: 7 (compared to 3 in February)

And now a few subjective reflections:

• I started really strong. The first week of this month I was an absolute machine. The routine felt incredible. I felt like a real writer. I was focused and energetic and just so goddamn writerly.

• Each week’s writing total went down. The second week was okay, the third week was spotty, and the last week was a travesty. 

• This decline was not super surprising. The first couple weeks of any new habit are always the easiest. It’s once the novelty starts to wear off that you really start to run into problems.

• I started to get distracted by work urgency as the month went on. I had several early morning meetings where it felt like I had to use the time I set aside for writing to prepare. I need to figure out a way to keep my intense job as constrained as possible into normal work hours.

• Even as my output tailed off across the month, I did a pretty good job getting up on time everyday. I would just sometimes get sucked into reading or looking at my phone or working on “regular work.”

• Finally, I started to wrap my arms around a large writing project in a way that I haven’t in a long, long, long time. I wrote around 7,000 words that I didn’t publish but I’m excited to keep nudging forward.

And a few more lessons (how is a “lesson” different from a “reflection”?):

• I created a process for daily writing that I’ve never used before but I really like. Basically, I create a separate file in Ulysses for each day. I then do all of that day’s writing in that sheet, regardless of the “type” of writing I’m doing. At the end of the writing session I can copy and paste what I created into it’s final resting space. For example, a typical day might contain a couple hundred words that are a journal entry that eventually lives in Day One, the first two thirds of an article I’m eventually going to publish on my website, and the beginning of an outline for an issue of The Deliberate. I’ll copy and paste these various chunks to the places they need to go but I’ll leave behind the “master” log of all the writing I do each day.

• It’s a really nice way to have a sense of progress since I can see each day’s note in the sidebar and see how many words I wrote.

• It lets me set myself up for the next day’s writing by ending each day’s writing session by creating tomorrow’s document and pre-populating it with my ideas or thoughts about what I could write about.

• The writing association with Tycho that I’m trying to build is slowly getting stronger. As I tailed off in my productivity last month I realized I had gotten sloppy with putting my headphones on and turning on Tycho as quickly as possible. 

I’m really looking forward to the day where I can make writing a larger part of my day job. The only way to do that, though, is to make writing a larger part of the rest of my life. Developing these skills and putting more of my ideas out into the world is what will allow me to eventually make that jump to more of a writing-focused career. The nice thing about my current writing routine, though, is that it’ll serve me just as well now as it will in this fictional future state where I can write all day. So, until then, if it’s between 6:15 and 7:30 in the Eastern American time zone then my butt should be planted in front of my desk, Tycho should be bumping in my ears, and I should be making words appear in Ulysses.

Month of Read

I have four Anchor Habits that I try to do everyday: exercise in some capacity, meditate, write something, and, most enjoyably, read something substantial. We’re now into May and I’ve given each of these habits (and writing twice!), except for reading, a month of their own. The time has finally come to rectify that. Welcome to the first Month of Read of 2020!

This month creates a bit of a conundrum for me. The basic idea was that although I try to do these four Anchor Habits in a minimal capacity everyday, I can be extremely hit or miss on them. I thought that by really focusing on one of them per month would help me get more consistent. And so far, that hypothesis has been right! However, I’m already incredibly consistent with my reading habit. As of this writing I’m rocking. A 62 day streak of having read at least 15 minutes per day. Reading is a part of my day that already feels like a reward and it’s pretty deeply baked into my daily routine.

So, what to do in a month where I’m supposed to really focus on it?

My initial inclination was to give myself a specific focus or restriction. Something like, I can only read fiction, or poetry, or I have to read something deliberately difficult, or read slower, etc. Something that would push me out of my normal comfort zone. However, for each of my other Focus Months where I was focusing on a habit for the first time, I kept it deliberately simple and basically just had the intention of, “Try to do the thing more than I normally would and see how you feel.” So, in the spirit of simplicity I’m going to do the same thing with this Month of Read. I’m just going to read as much as I can (which is kind of what I already do but I’m sure I can find some parts of my day where I could switch over from something low-quality, like browsing Twitter, to reading) and actually track the amount of time I spend reading in a time-based reading log (which is not something I normally do).

At the end of the month I’ll have a better sense of how much time I spend reading in a month where I’m really trying to spend as much time reading as possible. In the remaining two months of 2020 where I’ll focus on reading again, I’ll put some kind of variation or focus or restriction on the intention to make it more interesting.

Feel free to follow along in this Notion card to see how I’m doing during the month: https://www.notion.so/samspurlin/Read-as-much-as-I-can-every-day-3c855fdb064a43fa9e04577663543283

Carving Out Your Space to Contribute

Why do I sometimes feel ashamed of the stuff I like to read and write about? Is that shame trying to tell me something useful or is it keeping me from contributing valuable ideas to the world? 

Productivity Pornographer or Philosopher?

On the useful side of things, it’s definitely keeping me from participating in the “productivity porn” and “hustle porn” racket. There are definitely parts of my personality that are drawn to those topics in a way that I know isn’t helpful or healthy. I know that writing about productivity for the sake of productivity is not anything the world needs more of. There are too many people already hawking suspect productivity advice that papers over problematic views about the world and the role of work in our lives. I mean, I like reading and writing a good productivity hack as much as the next middle-aged white knowledge worker guy but that’s not exactly elevating the discourse about meaningful work. I like candy bars too but I’m not about to eat a candy bar only diet.

Speaking of elevating the discourse, I think that’s the other vector into my shame about what I feel drawn to write about. There are some folks who take an incredibly philosophical point of view and tone in writing about work and personal development that I find both admirable and completely unattainable with my writing and thinking ability. In my darker moments I look at someone writing and thinking at such a high level about this stuff that I feel like I shouldn't add anything if I can’t operate at that level. 

Considering I just articulated two ends of the same continuum, there’s obviously a lot of white space in the middle where I could probably feel pretty comfortable exploring. I know I’m not going to write absolute drivel about 10 productivity hacks to supercharge your productive productivity (even if I sneak a quick look at those articles from time to time...) and I’m not capable of writing a far-reaching philosophical treatise on the nature of work and the human condition. That doesn't mean those are my only two options, though.

Charting My Place in the Middle of the Continuum 

To stay away from the drivel end of the continuum, I think it helps to articulate that I specifically ascribe to a definition of productivity that’s broader than simply the amount of work you’re able to get done. It’s much more about overall meaningful engagement with the world — work or otherwise. It’s about feeling like an active agent in the world rather than a passive object. Anything from “tips and tricks” to life philosophies that help you feel more engaged with the world falls into the realm of productivity to me.

And on the other end of the continuum I don’t think it’s particularly helpful to keep the discourse around meaningful engagement with the world at the level that only philosophy professors can engage with. To the extent that I can use my experience in the academic world to bring those concepts and ideas down to a level that’s more digestible to the average person then I am providing a useful service. I’ve been out of the academic world long enough to know that what often passes as good writing in academia is utterly impenetrable to even very bright people and that making ideas accessible can be incredibly valuable.

As a reminder to myself and a public stake in the ground, these are the areas where I have something to contribute and I should be pushing myself to publish as much as possible on:

• Everything I’ve been thinking about with reformed workism and deliberate attention

• Everything I’ve learned about the reality of being an employee in an organization — legacy, self-managing, small, large, or otherwise

• The intersection of organization design and the individual experience of work

• The connection between using tools and software to make yourself a more effective agent in the world

• The remnants of my academic training in positive psychology and how it applies to individuals and organizations

• My own personal experiments/experiences with how I’m applying these concepts to my own life

Shame is the ultimate in unhelpful emotions when it comes to trying to make a positive impact on the world or do anything that remotely opens you up to potential rejection or judgment. For a long time I don’t think I really understood that a lot of my creative blockage was being caused by the shame I felt in either contributing to the anti-intellectual and unhelpful productivity hack genre or being unable to elevate my thinking and writing to the almost equally unhelpful “productivity philosopher” level. Now, I think I’m finally starting to realize that my advantage and gift is being able to explore much more of the continuum while staying away from either extreme end.

Shame and Comparison

In an effort to make this a little bit more generalizable and less navel-gazey, I have to imagine that this dynamic I just walked myself through is something that other folks experience, too. At its heart it’s a problem of comparison. The transparency of the internet has given us a much wider pool of people to compare ourselves to and believe it or not, there’s a lot of incredible people out there in the world. The most useful advice I’ve heard about this dynamic is that it’s profoundly unhelpful to compare your backstage to other people’s front stage. Meaning, you only have access to the polished final project that people project into the world (no messiness to be found anywhere!) whereas you're intimately familiar with all the personal discord that accompanies everything that you produce.

That’s why I love seeing “behind the scenes” content from the creators I really like. Show me your process. Help me understand that you don’t just crank out stuff that I adore with never ending productivity and effortless grace. Show me your struggle so that mine feels a little bit more normal.

Finally, the other piece of advice that I read somewhere a long time ago that sometimes soothes me in moments of uncertainty is that even if it seems like someone has already done what you’re trying to do, they haven’t done it in your voice. The writers and creators I follow most closely are not constantly sharing brand new ideas. Many of them cover well-trodden ground. However, it’s their voices and personalities that keep me coming back and interested in what they’re doing. That can be a difficult generosity to extend to ourselves but when I’m able to do so the quiet, doubting voice in my head is placated and I can actually focus on doing what I want to do.

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Personal development is an expedition, not an exercise in perfection

I don’t think personal development is an exercise in trying to reach some idealized state. Or at least, not some kind of universal idealized state that’s the same for everyone. I’m not interested in personal development because I’m trying to become more like somebody else who I think is admirable in some way. I’m interested in personal development because I’m trying to better understand and learn about myself. I believe that most of us only have visibility to a small sliver of our own personalities, capabilities, and general self-knowledge. Who “I am” is a bit of a black box, I think. I see the parts that are brought out of the shadows by the demands of my normal day-to-day life and the challenges I experience navigating it. But I get the sense that this is only a small portion — that there are parts of me that exist but I don’t regularly see or experience because they aren’t generally needed to navigate my normal life. I want to find those hidden parts. I want to understand those under utilized parts. And that’s why I pursue personal development. I want to see and understand and interact with the parts of me that are below the surface.

Or let’s try another metaphor on for size: an unmapped territory. The visible parts of me and my personality are like an extremely well-mapped neighborhood. There’s a ton of details on the map and it’s extremely precise. But as you get further from the center it starts to get a bit fuzzier. There aren’t as many road names and the features are more vague until eventually, once you get far enough away from that extremely well-mapped center, it simply shows fog and here be dragons. Personal development as I conceptualize it, then, is the systematic series of forays into that fog to update and add detail to the map that is me. It’s looking at that fuzzy map and the warning of dragons and asking, “Do there actually be dragons? Let’s see if we can find them.”

This is deliberately in contrast to a deficit view of personal development where I’m constantly trying to become better because I’m not enough. Or, because I’m not close enough to some sort of ideal person (or writer or athlete or consultant or whatever aspect of my identity isn’t feeling up to snuff at the moment). Approaching personal development from this angle is a qualitatively different, and I would argue less pleasant, experience. I’m certainly not immune from falling into this kind of comparative mindset. It’s easy to look at someone and immediately use them as some kind of measuring stick that almost always seems to find you wanting. That’s not a fun way to go through life and if you look at personal development through that lens I wouldn’t be surprised if it wouldn’t be attractive to you.

Limit work in progress in all the things — including your good intentions about yourself

But, let’s say that for whatever reason you’re already of the mind that personal development is an inherently rewarding experience and that being on a quest to better understand yourself is attractive to you. In my experience, one of the most difficult things about thinking this way is being overwhelmed by the options in front of you at any one time. And if your reading diet has as many non-fiction books in it as mine does you are constantly finding good ideas for things you’d potentially like to try. If you’re like most people, those ideas end up floating around in your head in some kind of liminal state for awhile until you eventually forget about them and go back to whatever your current default behaviors are. If your lucky, you might try something different long enough to slightly adjust your default behavior. If your like me, however, you’ll spend most of the time feeling like your failing at enacting new behaviors because you have too many in your head at once and no real clear commitments about what you told yourself you would do. 

Luckily, there’s a thought technology that comes from our understanding of how work flows through a system that I think is useful in this context, too: limiting work in progress. Somewhat counterintuitively, the most work in progress that exists in a system the less smoothly it flows through that system. By limiting yourself to less pieces of work in progress (with everything that still remains to be done waiting to be pulled from a backlog) you’re able to do much more than if you tried to do everything at once. This applies to personal development intentions, too. Trying to do everything at once is a recipe for frustration and for not actually changing much of anything.

A great tool for visualizing and limiting work in progress is a Kanban board. A kanban board is a simple tool for showing a list of work items sitting in a backlog, a list of work items currently being worked, and a list of work items that have been completed. These “work items” move from left to right through the system such that anybody can walk up to the board (or load it on their computer) and see the state of the system. They can see the work that’s yet left to be done, the work that’s currently happening, and everything that has already been accomplished. Why don’t we use this same idea for personal development endeavors, too?

What if instead of getting inspired by something you read in a book or article and immediately try to implement in your life (likely on top of whatever inspired you last week or the week before) you captured the idea and put it on a backlog? Then, on a regular cadence you could consult your backlog of ideas and promote a reasonable number to “active” status. As part of promoting something from the backlog you’ll also do some thinking up front to understand what it is you’re actually trying to do. Like a good scientist, you’ll have a hypothesis about what will happen and you’ll have a sense of what metrics you’ll need to look at to validate or invalidate your hypothesis. At the very least, you’ll know that on a certain date you will look at an experiment you were running and ask yourself a few questions like, “How did it go?,” “Did I learn anything about myself?,” “Does this tell me anything about what I should do next?”

That’s what I’m trying to create. An approach to help you capture, process, and implement personal development intentions so that you can come to better understand yourself over time. A system to help you keep from being overwhelmed with all the ideas you have about things you want to try or ways you think you could be “better” (however you want to define that word). By bringing some structure to this whole process I can spend more time and energy actually trying new things rather than trying to hold it all in my head. Holding it all in my head means I inevitably forget good ideas and almost guarantees that I feel badly about myself as I try to do a bunch of half-formed ideas/intentions at the same time — seeing very few of them to completion and generally feeling like I’m not doing “enough.”

Don’t (just) build habits, uncover insights about yourself

Over time, as I do more and more experiments/experiences I’ll occasionally shake loose an insight that helps me better understand myself. While these insights feel blindingly obvious when they occur to me, they’re also the type of thing that are likely to be forgotten faster than I would like. That’s why I want to capture them and keep them somewhere where I can regularly review them. This body of insights about myself and the world is my best articulation of who I am and a visual representation of my growing self-knowledge. It’s the map that I want to be adding more and more details to as I do more forays into the unknown.

The whole point of caring about personal development and doing experiments is to knock loose, uncover, craft, or otherwise get my arms around these key insights about how my brain works, what my personality is, why I think or believe the way I do, etc. These insights, then, can shine a powerful light on interesting paths to pursue in my personal development efforts. Which then creates new insights (or tweaks previous ones). The cycle continues. And because there’s no specific end point that I’m shooting for, no idealized state of perfection, I’m glad the cycle continues. The cycle itself is full of meaning and excitement.

Is finding joy in this cycle something that’s completely unique to me? Is it only interesting to a very small number of people who are similar to me? Or is it something that can be taught to anyone who has a little bit of curiosity about themselves and how they interact with the world? I honestly don’t know but this is the path of inquiry that I’m going to explore until I figure it out.

"Month of Sit" Recap & a Look at April

Is there a better time to try to develop a healthy meditation practice than during a global pandemic? 

My March focus for my Intensity/Simplicity theme was my meditation practice. As a reminder, I’ve decided to take each of my four daily habits (Read, Write, Move, and Sit) and focus on one at a time each month for all of 2020. January I focused on Move and tried to run a bunch. In February I focused on Write and tried to write a “shit ton.” March, then, has been focused on Sit.

Like with the other two months, I didn’t step into March 1st with a specific goal in mind. I figured for this first go around with each of the habits I would just try to see what it is like if I made a general intention to do each one “more.” In the case of January I think that worked pretty well. I definitely ran more than usual, at least. February was mostly a failure. I would put March somewhere between the two. As I sit here today on April 1st I see I have a 73% completion rate on actually sitting down and meditating every day. That comes out to 8 days missed out of 31. In February I missed 19 days so I definitely took a step in the right direction.

As part of this experiment I also re-read Mindfulness in Plain English to help ground me in what I was trying to do — and why. I did that in the first couple days of March with the vague intention I would read some other meditation-related books throughout the rest of the month but that never actually happened. I did re-subscribe to the Audio Dharma podcast and while I don’t listen to everything that shows up in that feed there’s usually at least one or two talks I’ll listen to each week. 

I did a combination of completely silent meditations using the app Enso as a timer and some guided meditations using Calm. The purist in me thinks the guided meditation craze ala Headspace or Calm or 10% Happier or Wake Up and the rest of the Relaxation as a Service companies is kind of a cop out and that you don’t “need” anything other than a place to sit and some quiet to meditate. However, in the absence of a teacher I do think I picked up a couple techniques via the guided meditations that helped. 

Finally, I had a vague intention to not only meditate “more than usual” but to find a place in my daily routine where it could become just an automatic part of my day. I played with a couple spots and I think I’ve landed on in the morning after I read/have coffee as my favorite timeslot with just before bedtime as a backup. I definitely learned that the later in the day it got before meditating the less likely I was to actually do it. 

Now, with all the arguably unimportant preliminaries out of the way, did I actually learn anything about myself by meditating more than usual this month? Honestly, no. But that’s okay. I have enough on-again off-again meditation experience to know that 30 days of extremely limited meditation (between 10 and 20 minutes a day) is not enough for anything to “happen” (to the extent that anything ever happens in meditation). I didn’t expect to become enlightened or have some kind of breakthrough — and I didn’t. I did notice that on days when I meditated I felt calmer and more in control of my emotions. I’m not sure if that’s a result of simply having done a thing I intended to do (I can get similar feelings from writing or reading or exercising) or was a result of the actual meditation experience itself. At the end of the day, it probably doesn’t matter.

April: Month of Write (Redux)

The nice thing about coming up with some kind of experiment or personal development program is that I get to make the rules. I had a general intention to spend the first four months of 2020 rotating through the four daily habits I mentioned earlier. Having done Move, Write, and Sit that would mean April is a Month of Read. However, I’m going to call an audible.

I’m still really annoyed about how poorly my Month of Write went in February, so I’m going to hold off on doing my first Month of Read and do another Month of Write instead. This time, though, I’m putting a little more structure into play. No more am I just going to vaguely try to “write more.” Instead, I’m specifically trying to sit at my desk and try to write from 6:15-7:45 AM everyday this month. The topic of the writing doesn’t really matter but the goal is to more or less keep my fingers moving for the vast majority of this time. Personal journaling and other stream of consciousness writing is what I’ll turn to if I’m not making any progress on an article for SamSpurlin.com or The Ready or The Deliberate or any other major writing project.

Basically, I’ve paid enough lip service to the idea of being a prolific writer and if I don’t figure out how to build it into my days, even though I have a very demanding day job, then I’m never going to figure it out. The day job may be demanding, but it’s flexible (and stands to benefit from my greater writing output, too). My life is also the simplest it’s ever going to be. It doesn’t necessarily get easier from here. I’m not married and I don’t have kids. If those things are in my future then it’s not like there’s some future writerly state where I’ll have more time or attention to dedicate to this. If I can’t lock in the practice now while I’m relatively free to do as I please then I’m worried I never will.

Along with the specificity of “sit at my desk from 6:15-7:45 AM everyday and try to write,” as a goal I’m putting in a bit more scaffolding to help me accomplish this.

First, I know my phone is the central character here who can foil my plans. If I look at email, Slack, Twitter, or Reddit before sitting down to write I’m much less likely to actually get it done. Therefore, part of my process is to not get my phone off its charger until after I’ve finished my morning writing session. The problem is that I generally use my phone as an alarm clock. However, with that setup I’m guaranteed to touch my phone mere seconds after I wake up; right when my willpower is lowest and I’m most likely to convince myself that looking at Twitter for a few minutes will “help me wake up.” The fix is simple enough, though. I bought an analog alarm clock so now I have no reason to touch my phone immediately upon waking.

Second, I can sometimes dilly-dally when it comes to making coffee in the morning. This is usually caused by getting lost in my phone but the resistance to getting up and actually making the coffee might be bidirectional with the phone problem. To that end, I’m making it as easy as possible to make coffee in the morning while still meeting my annoyingly high standards (fresh beans, pour-over or AeroPress) by filling the electric kettle the night before, putting beans in the hopper of the grinder, assembling the AeroPress or pour-over cone, and getting a mug out of the cupboard. It’s not much, but I’m hoping the fact that all I need to do is push a button and twist a knob to get hot coffee and prepped grounds will make it easier to actually get out of bed and to the kitchen.

Finally, I’m really taking seriously the idea that I can create an association with a specific type of music and a specific kind of work. I already listen to a ton of instrumental electronic music while I do other work and the band Tycho is my absolute favorite. When I sit down to write every morning I’m going to turn on my Tycho playlist and that’s the only thing I’m ever going to listen to while working (and I won’t listen to Tycho outside of these morning writing sessions, either). I’m hoping that I can get to the point where hearing a Tycho song immediately puts my brain into a state that’s particularly conducive to writing. 

I’ve been operating under this program for the last week of March and have been averaging somewhere between 2000 and 3000 words of fresh prose each morning — so the early returns are certainly promising! The trick, though, as with all monthlong experiments, is to keep this momentum going when getting up “early” and writing for 90 minutes is no longer the fun new thing and is instead “just a thing.” 

The End of My First "Month of Write"

Welp.

That didn’t seem to go very well.

My month of writing as much as humanly possible (actually, I guess I called it a “shit ton”) has come to an end and I can’t help but feel I mostly failed. Before the self-flagellation begins let’s start with the objective facts and then I’ll dive into a bit about what happened and what I think I learned.

This month I wrote approximately 6,000 words (plus whatever this article ends up being) spread across one issue of The Deliberate, one issue of Brave New Work Weekly, two published articles on Medium, and 10 journal entries. I did this writing spread across 13 days. The word output isn’t what’s getting me down — it’s the fact that I basically only managed to write for 50% of the days in a month where my primary focus was to write as much and as consistently as possible.

There were definitely some external factors at play that somehow didn’t manage to make their way into my daydreams about what this month was going to be like (funny how reality has a way nosing it’s way into everything). The past couple months have been perhaps the most hectic and stressful I’ve ever had while working at The Ready. I’m putting in far more hours than I want to be in order to make some (ostensibly) short-term projects successful. We’re expanding our scope at the client, I’ve been leading an initiative to work with external writers at The Ready, and my partner and I have been hiring and training a new member. I’ve also been on the road for much of the past month with trips to NYC, Charleston, SC, and Dallas, TX all happening in the past three weeks.

I don’t share these external forces as excuses. Only as useful context for understanding why it was difficult for me to accomplish what I had set out to do with this experiment.

I had hoped to build a set writing routine into my default day. Perhaps carving out an hour or so in the morning or maybe closing out my day with a strong writing session. I didn’t have strong feelings about when it happened, I just wanted to see myself prioritize writing every day. WIth a 50% completion rate that obviously didn’t really happen. I didn’t really stick with any specific time of day long enough to truly understand whether I could’ve made it work for me. I seem to find it difficult to write first thing in the morning but I’m so cognitively drained by the end of the day evening writing sessions don’t really happen either. It seems that the only way I’ll write as much as I think I could or should is if I bake it into the prime part of my day. Perhaps in calmer times that will be possible but when spinning as many plates as I was this month there was no way I was adding another plate without causing some catastrophic problems for myself.

It wasn’t 100% negative, though. One thing I learned over the past month was that I have an underdeveloped process — and respect — for the brainstorming, planning, researching phase of writing. Early on I wasn’t giving myself credit for days where I simply outlined a potential article or pulled together notes but I quickly realized that was stupid. Writing is more than sitting down and drafting prose and if I don’t give myself mental credit for doing the stuff that allows me to draft then I’m shooting myself in the foot for no good reason. Along with the mental permission to consider outlining/mind mapping a legitimate part of my writing process I also realized I don’t really have a robust process for taking an idea from a nugget to a fleshed out article.

My bailiwick is smallish ideas that can be captured in 1,000–2,000 words. A blog article, basically. I don’t want to just be a blog article writer, though. I want to be able to push an idea across many writing sessions and many rounds of revisions before I share it with the world. If everything I write has to be conceptualized and drafted over the course of one working session then I’m really putting a ceiling on the type, amount, and quality of the writing I can produce. I think I have a newfound respect for figuring out how to do all the work that surrounds a productive session of actually making prose appear on the screen.

In my remaining two “Months of Write” that I have in 2020 (tentatively scheduled for June and October) I have a couple ideas that I’m batting around.

1. Shooting for a specific word goal.

2. Working on one “piece” of writing the entire month.

3. Picking a specific part of my day and making the focus of the month the installation of a writing routine in that part of the day.

4. Forgoing all public writing for the month and just exploring ideas in complete privacy for a month.

While my guardrails for this month were deliberately broad and pretty vague, I’m wondering if I might benefit from some tighter constraints the next time around.

And while I didn’t hit 100% on this month’s aim of writing everyday I do feel like I learned some things about how I can become a better writer and I’m looking forward to taking another crack at it in a couple months.

I’m Sam and I write about time and attention at The Deliberate and help organizations become more adaptive at The Ready. I Tweet and post really mundane pictures on Instagram.

In February I'm Going to Write a Shit Ton

Month of Focus #1 is done and in the books. Over the course of January I focused on my daily habit of getting some sort of exercise. Specifically, I tried to walk and run as much as I could. It wasn’t a perfect month but I did manage to have a relatively high level of consistency and saw myself improve across a couple metrics.

Moving onto February I’m shifting my attention to a new daily habit, writing. I have long known that I am a better version of myself when I’m writing consistently. Of all the potential creative outlets I could do it’s definitely the one I’m most skilled at and derive the most satisfaction from doing. It acts as the best conduit I have for channeling diffuse feelings of unease or frustration or confusion into something more useful. Just as nobody has ever regretted going for a run or getting some exercise I’ve never regretted spending some time writing.

While the therapeutic benefits of writing are real and valuable enough to make it an important part of my daily routine on its own, writing has also been the cornerstone of nearly every good professional thing that has happened to me. Or at least many of the good things that have happened. I definitely got into grad school on the strength of my writing. I definitely got an interview at Undercurrent back in the day because I had a large body of writing to point to when my actual consulting experience was lacking. Most of the “big breaks” that have happened in the transformation projects I’ve worked on have happened after I sat down and wrote a heartfelt letter to the client about what was going on and what I thought we needed to do.

When I think about the evolution of my career I know that I want writing to play a larger role in it. I love the consulting work I do right now, but I’m not sure I’ll love it forever. I want to write books. I want to write articles for my own website and for magazines and for anywhere else where smart writing is regularly being published. I look at someone like Ben Thompson as both a professional and intellectual role model as someone who makes an independent living primarily off the strength of his writing.

Words are my friends and writing is a salve for my anxious mind.

And just like my real, flesh and blood friends, sometimes I don’t do enough to invite them into my life as much as I should.

So, here I am sitting down and saying that for the month of February I’m gonna write as much as I can. I’m not here to set a bunch of specific goals or make any grand pronouncements about what I will have produced at the end of the month. I just want to spend more time writing this month than I normally do. Just as I had some simple guardrails for last month’s experiment (try to run/walk a lot, everything counts, listen to your body and don’t get hurt you idiot) I need to develop some guardrails for this month:

• Write everyday — even a little bit

• Don’t worry about hitting a word count

• If you have extra time, energy, or attention, write

• Public writing is good

• Private writing is good too

• Try to do it early in the day but don’t be precious about it

That should help keep me on the straight and narrow, methinks.

And since this is a bit of a visioning/chartering exercise, let’s capture some hypotheses about how I think this month is going to go or what I might experience over the next few weeks:

• The first week is going to be fun and I’m gonna write all sorts of stuff that I end up sharing with all of you and feeling really proud and happy about it

• After the first week I will have exhausted all the really low hanging fruit that I was excited to write about and it’s going to start feeling like a pain in the rear

• I’m going to end up writing some really weird shit at some point

• Hopefully I’ll break myself out of the habit of only writing things that I can draft and edit in one working session and instead work on some stuff that takes longer to do

• At the end of the month I will have written more than I probably have in years and I will also be willing to move onto my next Focus Month

My plan is to keep adding to this Twitter thread with everything I publish over the next month. That’ll be an easy way to follow along if you’re curious about what a focused month of writing ends up looking like.

My name is Sam and I like words. I write them here and at The Deliberateand on Twitter. I also say them into a microphone on my podcast, Fields of Work.

Introducing Focus Months

My yearly theme is Intensity/Simplicity. I want to do intense things but I want to do them simply. I’m not interested in getting intense about details at the margins. I’m much more interested in marrying intensity with the essence of a thing.

As part of this intention I’ve decided to take my four Anchor Habits (daily writing, reading, exercise, and meditating) and focus on each of them for a month at a time. With four habits and twelve months in a year, I’ll have an opportunity to go deep with each of them three times in 2020 (yay math!)

The idea is that I’ll continue to do my three other daily habits at a consistent, yet minimal, basis while I use whatever extra attention/energy/motivation I might have to really go deep with the chosen habit. I have a couple ill-formed hypotheses I’m pretty sure I’m testing:

• Focusing on one intention for a month will help me uncover new levels of appreciation for it.

• The more interesting experiences lay below the surface (i.e. after you focus on it for longer than a day or even a week)

• Limiting the number of personal development decisions I need to make will leave more time and energy for actual personal development.

• Doing one thing for a month will mean I’m tired of that thing by the end of the month and will have lots of motivation and excitement to do the next thing.

That’s the plan.

January — The Month of Move

I decided to kick this experiment off by focusing on my daily exercise habit (or as I tend to call it, my Move habit). The basic idea was that I would try to run, walk, or otherwise exercise as much as I reasonably could throughout the month of January. I had a couple guardrails in place:

• Speed doesn’t matter.

• Walking counts.

• Consistency even over session-level intensity.

• Listen to your body — don’t get hurt you idiot.

So, what did I actually do?

• Walked or ran 52.79 miles

• Did an hour and 42 minutes of strength workouts

• Did just over an hour of yoga and foam rolling

• Played in 3 hockey games

• Had 7 “zero days” (where I did nothing)

In the middle of the month I got sick for a couple days, but surprisingly (stupidly?) still managed to go for a walk on each of those days. I only really got waylaid in my plans to workout consistently in the last week of the month when I had some really intense responsibilities at work. It wasn’t ideal to string together a series zero days right at the end of the month but if we consider February 1st to be an honorary member of January then I actually ended pretty strong.

Overall, I feel pretty good about this first foray into what I’ve now decided I’m going to call Focus Months.

Other than the work week from hell I was able to keep a pretty high level of consistency all month. Perhaps most surprisingly, I actually saw myself improve my running (objectively and subjectively) even across the relatively short timeframe of a month. I started looking forward to my runs and even managed to go for significant stretches where I wasn’t hating every step.

One of the things I’m keeping an eye on during these Focus Months is whether focusing on one specific habit or area of personal development might have impacts on other parts of the complex system that is me and my life. I noticed I had an easier time being more mindful of my eating (in both food choice, portion size, and consistency of tracking) than usual. Knowing that I wanted to workout more than I normally do made it easier to put somewhat better fuel in my body on a consistent basis. I’m guessing each type of focus will have somewhat unexpected spillover effects with other parts of my life.

I’m going to chalk up this month as a success and put my focus toward my next Focus Month, writing.

I’m Sam. I write about attention at The Deliberate and I help organizations at The Ready. I help nobody on Twitter.

How to Engage With an Overwhelming World

What’s the best way to navigate a world of infinite information? Should we manually create highly curated informational ecosystems for ourselves or should we dip in and out of the overwhelming stream while trusting algorithms to surface the interesting, relevant, and necessary? Is there a clear best answer for everyone or is it a matter of personal taste? Does it hold true across all types of information, or can you vacillate between these two approaches depending on the source?

When thinking about different ways to engage with the world I think you can plot them on a 2x2 graph where the two axes are Algorithmic Curation to Human Curation and Few Sources to Many Sources. The Algorithm/Human axis describes the way in which you decide what to engage with. On the Algorithm end of the continuum you’re relying on recommendation algorithms to learn your preferences and serve up the most relevant and interesting content automatically. These are things like following people Twitter recommends to you, using the first-party Twitter app with it’s algorithmic (rather than chronological) timeline, and letting YouTube recommend the next video you should watch. On the Human end of that continuum you have the individual practice of deciding what to engage with and how. This is things like using a third party Twitter app (like Tweetbot) that allows for a purely chronological timeline, being extremely selective about who you follow, and having only a set number of news sources that you turn to for information (like a home delivered newspaper or a specific magazine).

The other axis describes the amount of informational sources you will consider when designing your informational ecosystem. Folks on that end of the continuum are simply interacting with very few sources of information whereas folks on the other end of the continuum tend to surround themselves with many different sources of information or interaction.

You can then take the 2x2 chart and describe each of the quadrants: The Surfer (Algorithmic & Many Sources), The Minimalist (Human Curated & Few Sources), The Uninformed (Algorithmic & Few Sources) and The Overwhelmed (Human Curated & Many Sources).

To better understand to more interesting Minimalist and Surfer approaches, let’s take a quick detour into The Uninformed and The Overwhelmed, first.

The Uninformed

The Uninformed has the mindset of The Minimalist but the approach of The Surfer. They have a small number of sources that they don’t ever really engage with and haven’t really curated. They mostly go through the world without really thinking about the informational ecosystem around them and without having ever made deliberate decisions about what to pay attention to and what not to.

The Overwhelmed

On the other hand, The Overwhelmed is interested in many different sources of information but they try to engage with them on a purely human curation level. Meaning, they probably spend most of their time being distracted and deathly afraid of FOMO. They don’t want to miss out on anything so they are constantly engaging with everything all the time to make sure nothing slips through the cracks. It looks manic and desperate and is a guaranteed path to burnout.

The Minimalist

The Minimalist practices extreme curation around the information she lets into her life. She’s generally not interested in having algorithms provide recommendation or curation. It’s all about reducing the sources of information as much as possible and keeping the vast majority of the noise outside of her well-curated cocoon. It’s all about engaging deeper with fewer things and doing everything within her power to not be distracted by anything new and shiny. Occasionally a new source of information may wiggle its way into her consciousness, but that is a relatively rare occurrence.

This approach gives you an intense sense of control. Since your informational ecosystem is so limited it’s easy to feel like you’re “caught up” or “up to date” (as long as you don’t think too much about all the potential sources of information that aren’t part of your system). Distractions tend to be fewer and infrequent which allows for a narrower or deeper appreciation for the sources of information and topics you follow (e.g. reading The Economist from cover-to-cover versus browsing your Twitter timeline).

On the other hand, though, it can be surprisingly easy to get obsessive about curation. Since the larger informational ecosystem is outside of your control you’re constantly having to re-evaluate whether something new could or should become part of your limited suite of information. Additionally, even if you only follow a select few sources of information it can be surprisingly easy to get overwhelmed (how many people have died under the ongoing crush of a single New Yorker subscription?)

The Minimalist approach often means forgoing the potential for new connections (both in terms of people and ideas). It’s not about looking widely at all the available sources of information or potential connections. It’s about figuring out the bare minimum of information you need to get by and then basically ignoring everything else.

The Surfer

The other approach to navigating our overwhelming world of potential information is to embrace the immensity of the situation and deliberately “surf” along the top of it. The Surfer embraces algorithms as the best way to surface relevant and interesting information. He may follow thousands of people on Twitter or Instagram but doesn’t worry about being any sort of “completionist.” They dip into the stream from time to time as the situation dictates it.

The Surfer commits to nothing. Everything is potentially available to him and he trusts the algorithms and AI to show it to him at the right time, regardless of the source. He wouldn’t subscribe to The Economist, but he would read an article from The Economist that someone recommended on Twitter or showed up in Apple News.

This approach has less overhead than the Minimalist. He doesn’t have to spend time evaluating and vetting and testing various sources for inclusion into his highly curated life. He just has to occasionally push the Like/Dislike, Thumbs Up/Thumbs Down buttons to feed the algorithms along the way. He’s constantly being exposed to new things (well, within the confines of his specific filter bubble) and can more easily make new connections between ideas and people.

The Surfer, however, is at extreme risk of getting distracted and sucked into unproductive uses of time. The algorithms he trusts to elevate the relevant and interesting can often easily overcome his willpower. The services who provide and design these algorithms are not interested in giving him just the right of information and sending him on his way. They want to consume as much of his attention as possible and will do anything to get it.

In addition to a real sense of “playing with fire” The Surfer is at risk of creating a filter bubble around himself. The algorithms that are trying to extract as much of his attention as possible aren’t interested in showing him things that might turn him off or cause him to do something else. The Minimalist, on the other hand, can deliberately choose to incorporate sources of information that run counter to her general inclinations or beliefs in an effort to have a more well-rounded view of the world.

I’ve tried to write about both of these approaches in a very even-handed way because I actually think both can be incredibly valid ways of interacting with the world. They each have pros and cons (probably more than I’ve described above) and they both can be used productively and successfully. If that’s the case, though, how do you choose which one is best for you?

I’ve found myself vacillating between the Minimalist and Surfer approaches over the past few weeks and I’m planning on diving deep into the pros and cons of each of these approaches in future articles. In the meantime, though, I’m curious about how you think about creating your informational ecosystem. Is this framework interesting? What would you like to see me (or someone else) explore with it?

Hi. I’m Sam and I write about attention and work and organizations. Follow along on Twitter and maybe subscribe to my newsletter, The Deliberate?

The Year of Intensity/Simplicity

In lieu of a New Year’s resolution I like to select a theme to help guide me over the coming year. A theme is kind of like a resolution in that it is an attempt to somehow be different (maybe even better!) than I currently am but it differs in that it lacks the clarity or specificity of an actual goal.

This is by design since the downfall of my previous attempts at picking and sticking to a New Year’s resolution always seemed to hinge on the fact that what seemed urgent and important on December 31st lost its potency by the middle of summer (if it was lucky to last even that long). A year is a long time to focus on one specific personal improvement intention so I’ve experimented with a shift to a yearly theme over the past few years.

The nice thing about a theme is that it’s broad enough to apply in many different situations. If done right, it acts as a filter that all your decisions and experiences go through. It’s like wearing sunglasses all the time — your eyes are protected by the dark glass and eventually you just kind of forget they’re there. I mean, your theme shouldn’t fade entirely into subconsciousness but you don’t really want to be thinking about all day everyday, either. Instead, it just acts as a guardrail to help keep your decisions headed in a way that they may not go otherwise. And other times it’s like a helpful and cheerful parrot sitting on your shoulder and constantly asking, “Does this align with your theme? Does this align with your theme? Does this align with your theme?”

Anyway, enough about themes. They are good and you should pick one (or two).

Last year’s theme was The Year of Deliberate and I wrote about it a whole bunch in another article. You should read it. It ended up being extremely successful and helpful.

Now, onto this year’s theme.

I’m not a very intense individual by nature (in most, but not all, things). I was a pretty good youth/teenage hockey player but looking back at my career with the benefit of hindsight I can see that I wasn’t really that intense (at least by elite hockey player standards). I wasn’t a particularly intense student. I was lucky to get by on natural talent in most things and could work hard when that wasn’t enough. But working hard isn’t intensity. Even now, in my work as an organization design consultant and writer I can see large swaths of my day-to-day work where I could benefit from doing what I’m currently doing… but in a slightly more intense way.

Over the past few months I’ve been trying to notice when I find myself intrigued or repelled by somebody in a social or professional setting. Almost universally I’ve realized the people I find the most interesting in most settings are intense about a thing (or at most, a couple things). When you talk about the thing with them you see them find another gear. They scoot to the edge of their seat or set their drink down so they can more move their hands around with greater theatrics or they start drawing things on scraps of paper — you get it.

You might think the opposite of this would be people who are super calm and chill all the time. I don’t think that’s quite right. I think the opposite of the intense person is the person who just doesn’t care about much of anything. No strong opinions. Somebody who couldn’t talk your ear off about a thing (even if they think you’d think the thing is boring — I love when people have obsessions over weird stuff).

Just to be clear, on this continuum of INTENSE to MILQUETOAST I think I fall more toward the intense end than the bland end. Anybody who has gotten me going about GTD or the Detroit Red Wings or org design or whatever sci-fi book I happen to be reading at the time know that I can pour on the intensity from time-to-time. There’s something about the last couple years, though, that make me want to take this dedication to intensity more seriously.

I think it may come from a sense of doing too many things at too mediocre of a level. I love being busy and I love new projects and I have a hard time telling anyone (especially me) no. It’s hard to be particularly intense about a few things if you have a ton of stuff going on, though. Looking at it through this lens, then, I realize that I want to try to say yes to fewer things and then do them with a newfound intensity.

But I also want to explore intensity in other parts of my life. How do I up the intensity in my relationships? What does it look like to be an intensely attentive partner? An intense son? What does it look like to bring intensity to a conversation with a stranger and a conversation with a lifelong friend? What topics would I want to broach, how would I want to show up emotionally, how can I be a better version of myself by turning up the intensity a little bit?

And what about my personal habits? What would a more intense commitment to health look like? More intensity with my writing? With meditation? With committing to simplicity and minimalism?

The nice thing about this theme is that I’m not really undertaking it as a grand effort of fundamentally changing myself as a person. I actually think I’m pretty great. I do work hard. I do care about people. I can be empathetic to a fault. I want to do the things I already do… but I just want to do them better.

But wait, there’s more.

I could wrap up this article right here and call it a day but I think I want to try something a little different this year. With a single word or concept yearly theme you can run the risk of over-indexing on it. I’m sure it doesn’t take too much imagination to see how I could potentially go off the rails with a yearly theme of “Intensity.” For that reason, and because I like the idea of a partially paradoxical yearly theme, I’m going to add another word — “Simplicity.”

Simplicity is about operating from first principles whenever possible, removing unnecessary distractions, and staying as close to the essence of the thing as possible. Intensity without simplicity could be disorganized. Intensity with simplicity is focused. Intensity without simplicity could have you chasing rabbit trails — intensely. Intensity with simplicity means doing the right thing consistently.

On the other hand, you can look at simplicity as being in opposition to intensity. A lot of times the simple thing is the easy thing and very rarely is the easy thing the intense thing. In my case, I think it will be helpful to filter my desire for intensity through a secondary lens of simplicity. I’ve already seen some very early positive returns that this dual focus can have. In the middle of December I decided that I was tired of seeing my yearly weight graph ever steadily going up and to the right. Like many folks at the end of the year I decided that 2020 was going to be a year where I took my fitness more seriously.

I had already been noodling on this Intensity/Simplicity theme for a little while at that time so my first impulse was to ask myself what it would look like to get intense about my fitness. All sorts of things started coming to mind — getting a trainer, finding the best gym, finding some sort of elaborate program to follow, etc. However, once I added simplicity to the equation I realized that I would be better served by directing my intensity into as simple a plan as possible (namely, eat more reasonable portions and run). I’m still being intense about it but I’m actually being intense about the right things rather than something ancillary like joining a dope gym or hiring a trainer.

I’m looking forward to navigating this creative tension throughout the year. Asking myself whether a given decision or situation is calling for my simplicity theme or my intensity theme — or perhaps a hybrid of both — is going to be a lot of fun.

What does your upcoming year look like? What’s your theme?

I’m Sam. I help make the future of work more human and adaptive at The Ready. I help humans take back their time and attention at The Deliberate.

Looking Back at a Year of Growth, Grief, and Calm

In 2019 I tracked (deep breath): sleep duration, sleep quality, the average time I went to bed, steps, running + walking distance, body weight, number of meditation sessions, duration of meditation, heart rate (average, waking, and exercise), the amount of time spent on each of my devices, the number of times I picked up each of my devices, the number of journal entries I wrote, number of workouts, days of reading at least 15 minutes, days I wrote, the video games I played, the TV I watched, the movies I watched, the number of flights I took, the number of miles I flew, the number of airports I visited, and the music I listened to the most. Before you write me off as a complete lunatic, I did all of this with a weekly routine that takes no more than fifteen minutes every Sunday morning. Almost every single metric on this list was passively collected by the various devices, apps, and services I surround myself with. My role was simply pulling it together into a spreadsheet each week so I could see patterns and interact with the numbers enough to get a feel for what was going on.

When I sat down to plan this article I saw two clear paths in front of me. The first path was to dive deep into the numbers for each metric. I have the numbers so why not cleave as close to them as possible and stay firmly in the realm of the objective? The other path is to let the data I collected over the year act as the background music for some more subjective reflections. Part of me thinks that’s a waste of perfectly good data but I know, actually, that this is the more meaningful way to do a yearly retrospective.

For the past couple weeks I’ve been marinating in everything I collected over the past 12 months. In some cases I’ve been liberating it from apps that aren’t part of my weekly metric collection routine (Goodreads, Flighty, etc.) and in other cases I’ve been looking for patterns and stories that are living just under the surface of the numbers themselves. With all these numbers starting to settle, like a snow globe coming back to its rested state, some insights are becoming clearer. Feelings about what went well and what didn’t. What over the past year brought me a sense of accomplishment and what is tinged with shame. The things I look back upon fondly and those events and activities that my self-protective ego has already expunged from memory.

My aim is to marry these two spheres of experience — the subjective and the objective, the emotion and the data, into a coherent sense of what I experienced over the past year. With this, then, comes the ability to feed and grow the aspects of this year that I want to carry into 2020 and hopefully avoid repeating mistakes of 2019.

Revisiting 2019’s Theme

Without rehashing last year’s article where I go into the weeds about why I selected this as my theme, the basic idea was that I wanted to spend the year doing “everything” more deliberately. I had noticed some bad habits starting to take root that all orbited around a lack of focus, concentration, and just an overarching sense of floating through my days. The aim was to have a theme that helped eliminate the float and instead anchor myself in deliberate action.

The centerpiece of last year’s theme was something I ended up calling Anchor Habits; the four daily habits that are necessary for me to feel good about any given day (read something substantial, write something, meditate, and engage in some kind of deliberate exercise). I tracked each of these behaviors all year long and gave myself an “Anchor Point” for each one I completed; which means each day could have a potential of four Anchor Points. If I successfully hit all four Anchor Habits in a day I called it an Anchor Day and tracked that, too.

A couple lessons from trying to do this for a full year. First, I was right that these four habits are the bedrock of a good day. When I did them I felt good about myself and the world. When I didn’t do them I felt off. Second, it was surprisingly hard to hit Anchor Days. Most weeks I only had one or two. Some weeks I had none. I had a perfect seven Anchor Days in a week only once.

This focus on Anchor Habits was a key component of my Year of Deliberate, but it wasn’t the only thing I did in 2019 to try to teach myself to have more control over my attention. A couple other highlights include starting a newsletter about “managing attention in a complex world” (conveniently titled The Deliberate), continuing my practice of recurring office hours (a way for me to deliberately practice connecting with strangers in a short period of time and building my network), dabbling with “hyper scheduling,”and starting a podcast with my brother where we explore our vastly different experiences in the world of work.

Each of these projects, in different ways, were exercises in becoming more deliberate. More deliberate with my time, my writing, my community, and in spending time talking to my brother.

The thing about a yearly theme, rather than a new year resolution, is that it’s supposed to permeate across your life. It may spark some discrete projects, as it did for me, but it is a background process that’s running in the back of your mind at all times. Ideally, it’s subtly influencing decisions in conscious and subconscious ways throughout the entire year.

The rest of this article I’m going to share some reflections and data that seem separate from the Year of Deliberate, but probably aren’t if I were to hold them up to the light for closer examination.

Overarching Feelings from 2019

Pride in professional growth

In many ways 2019 was a banner year in my own professional growth. After a very up-and-down 2018 (difficult project with a ton of travel, a longer than planned idle period that messed with my confidence, etc.) I felt like I was the most on top of my game I’ve ever been. I can’t go into too much detail without violating client confidentiality, but basically I was very successful in selling the work The Ready does at a very large organization that sorely needs the help we provide. In addition to having my first taste of success in selling a substantial amount of consulting work, I acted as the “lead” on the project for much of the year. This isn’t an actual role that we have at The Ready but because of some creative staffing we had to do in the middle of the year I was more or less the common anchor that held the project together during that time. This has challenged and pushed me in ways that were brand new but also have made me a much more confident and capable consultant.

A brush with grief for the first time

I’m a very fortunate 32 year old. There has been very little personal grief in my life up to this point. Both of my parents are relatively young and healthy. While I have lost a grandmother, it was when I was a baby and too young to remember (and my grandpa remarried a woman who is the only grandma I’ve known). This changed in 2019 when we lost my Grandpa Ed in October. While not entirely unsurprising (he was 93) it was still a very intense and very sad time — both the couple of weeks leading up to it and in the immediate aftermath.

I had never been faced with that kind of grief before and I feel like it opened up a part of me that had never been exercised before. It brought me closer to family, gave me a much more intense appreciation for life, and opened me up to talking about emotions that I’ve never before let out.

Comfort and joy in routine

Looking back at 2019 I’m struck with how calm it was in comparison to other recent years. 2015 was marked by the decision to move from California and start work with Undercurrent (and then The Ready) in New York City and all the tumultuousness that moving across the country and starting a new job entails. 2016 and 2017 were years of learning how to live in NYC, learning how to be an organizational consultant, deep impostor syndrome, keeping a long-distance relationship alive, tons of travel, and generally drinking from the firehose of experience. Late 2017 meant moving to another new city (Washington D.C.) and 2018 meant 6 months of full-time commuting to San Francisco followed by 6 months of physical and emotional recovery that the previous 6 months demanded. Compared to the previous four years, 2019 was downright calm. Working on a predominately local client meant my travel was drastically reduced. With my travel drastically reduced I was able to form a daily and weekly habit that helped me stay centered and productive most of the year. In these routines I have found more joy, calm, and stability than I have in a long time.

Meaningful Data from 2019

Moving out of the realm of the subjective and into the world of data, here’s what stood out to me from 2019.

Less reading, but very okay with it

I know I read a lot. Part of me is afraid that even writing this section comes across as some kind of humblebrag because I know I have to be in the 1% of folks with how much reading I do. Nonetheless, I think there’s something interesting worth diving into with regards to my reading stats from last year.

In the last four years I’ve finished the following number of books: 62 (25,188 pages), 72 (26,215 pages), 60 (20,562 pages), and 75 (24,509 pages). In 2019, I read the fewest number of books (60) and pages (18,518) since I started tracking. What’s notable about this number is the feeling that it elicits (or doesn’t) within me. Namely, not much. In fact, I’d be very okay seeing that number go down in 2020.

Up to this year, I think I read almost compulsively about topics related to my field of work. I felt behind and out of my league with basically everything I was doing so reading — and the fact that I could do it quickly — became my biggest and best weapon for getting up to speed. So, for the past four years I’ve read voraciously and borderline compulsively. 95% of those hundreds of books have been non-fiction and read at a sprint. I’m done with that, I think. So done, in fact, that I bought myself a subscription to Blinkist and I’m going to try to do as much of my non-fiction “reading” there as I can. Instead, I’m going to shift as much of my reading as possible into the realm of fiction and let myself take a bit of a breath and a beat when it comes to non-fiction books related to my line of work.

Up in exercise — but also up in weight

2019 was the first year where I started tracking whether or not I did any “deliberate exercise” in a given day. The definition of “deliberate exercise” was left pretty vague and I allowed it to have a pretty low bar. A walk counted. Getting a massage counted. A “real” workout obviously counted. Basically, I wanted to string together as many days as possible where I made a deliberate decision to do something at least moderately physical. I ended up giving myself credit for 223 days where I did just that.

What this didn’t translate into, however, was improved health. In fact, I continued my ever so gradual yet consistent trend to getting heavier (from 2015–2019 I’ve averaged 203.6 lbs. to 207.4 and currently weigh around 210). I’m going to continue this tracking into 2020 but I think the main takeaway is that I can’t expect this to be enough to lose weight or be particularly healthy. Making a bare minimum decision around doing some kind of daily exercise is table stakes and I need to bump it to a slightly more intense level, and take a look at my eating habits, if I want to end this troubling bodyweight trend.

I should write more — but I actually wrote a lot?

One of the most ubiquitous feelings I live with is the never ending sense that I’m not writing “enough” (whatever that means). My professional identity, to the extent I had one before and during grad school, was mostly as a writer. I wrote literally hundreds of articles on the various incarnations of my website over the years from 2009–2015. Ever since starting work with The Ready my writing output has fallen off a cliff (having a demanding full-time job can do that to you). Somehow I have failed to adjust my personal expectations to account for that. As a result, unless I’ve recently published something there’s a good chance I’m mentally beating myself up for not writing more.

This is where a robust year-end retrospective process can come in pretty handy. As I was going through all my data from the last year I realized I wrote 8 articles for my personal Medium account, 2 articles for The Ready’s publication, 35 issues of The Ready’s newsletter, and 26 issues of my newsletter, The Deliberate. That’s not even including the 118 personal journal entries I wrote throughout the year, too. There’s no way I can look at that output and keep up the story that I don’t write. Could I write more? Of course (and I intend to in 2020). But should I be beating myself up as if I didn’t publish anything this year? Of course not.

Conclusion

I could probably write a paragraph or two about every category of data I’ve collected over the year. That would be interesting to a grand total of one person (me) so I think I’ll wrap up this year’s review here. If you’re interested in taking a look at the spreadsheet I used to collect most of my personal data this year, you can check it out here. If you see anything interesting or want to ask any questions, please shoot me an email (samspurlin@gmail.com) or catch me on Twitter (@samspurlin).

Now that the review is more or less finished, it’s time to decide how I want to use this information to steer my behavior and intentions in 2020! I’ll be sure to link to that article here once I finish it. In the meantime, thanks for indulging me and good luck in 2020!

My name is Sam and I help organizations fight bureaucracy at The Readyand people fight for their attention at The Deliberate.